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Puerto Rico Cruises Starting In October 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in October 2027 or 2028, we have 12 unique cruise itineraries and 135 departures available, operated by six of the world's leading cruise lines departing in October.
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12 Cruises (135 Departures)
12 Cruises (135 Departures)
Departures
Duration
8 Days
16 Days
Countries Visited
Start & End Cities
Ship Size
Ship Features
Operators
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Price
$500pp
$28,620pp
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13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (2)

13 Days (12 Nights) Barcelona to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visits: Spain, Morocco, Puerto Rico
Inside
$1,550
Oceanview
$1,725
Balcony
$1,899
Suite
$6,425
From (Per Person)
A$1,550
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2029
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$865
Oceanview
$1,071
Balcony
$1,112
Suite
$1,617
From (Per Person)
A$865
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$636
Oceanview
$774
Balcony
$1,022
Suite
$2,309
From (Per Person)
A$636
Save 16
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Jun 2027 to Oct 2028
Visits: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,329
Oceanview
$1,454
Balcony
$1,474
Suite
$3,060
From (Per Person)
A$1,329
Save 1,117
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departure: 31 October 2027
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$2,257
Oceanview
$2,263
Balcony
$2,598
Suite
$4,304
From (Per Person)
A$2,257
Save 1,204
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (6)

10 Days (9 Nights) New York to San Juan
Operator: Azamara
Ship: Azamara Quest
Departure: 28 October 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,835
Oceanview
$3,286
Balcony
$4,030
Suite
$6,902
From (Per Person)
A$2,835
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Sep 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,047
Oceanview
$1,109
Balcony
$1,675
Suite
$2,246
From (Per Person)
A$1,047
Save 895
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visits: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,562
Oceanview
$2,869
Balcony
$3,413
Suite
$5,779
From (Per Person)
A$2,562
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,521
Oceanview
$1,593
Balcony
$1,797
Suite
$5,584
From (Per Person)
A$2,443
Save 40
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,149
Oceanview
$1,232
Balcony
$2,389
Suite
$3,095
From (Per Person)
A$1,149
Save 677
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Princess
Ships: Star Princess, Sun Princess
Departures: Oct 2027 to Jan 2029
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$816
Oceanview
$994
Balcony
$1,133
Suite
$1,509
From (Per Person)
A$816
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 23 October 2027
Visits: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,845
Oceanview
$2,003
Balcony
$2,090
Suite
$4,151
From (Per Person)
A$1,845
Save 987
Per Person
View Trip
Results: 12 results

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